N-pyrazolyl anilines as pesticides

ABSTRACT

The present invention relates to new N-pyrazolylanilines and N-pyrazolylaminopyridines of the formula (I) ##STR1## in which R 1 , R 2 , R 3 , R 4 , X, Y and Z have the meanings given in the description, to processes for their preparation, and to their use as pesticides.

This application is a 371 of PCT/EP95/00416, Feb. 6, 1995 nowWO95/22,530.

The present invention relates to new N-pyrazolylanilines andN-pyrazolylaminopyridines, to processes for their preparation, and totheir use as pesticides.

It is known that certain N-heteroaryl-2-nitro-anilines such as, forexample, N-1,3-dimethylpyrazol-5-yl!-2,6-dinitro-4-trifluoromethylaniline and N-5-trifluoro-methyl-1,3,4-thiadiazol-2-yl!-2,6-dinitro-4-trifluoro-methylaniline,have fungicidal and insecticidal properties (cf. EP-A-0 478 974, WO93/19 054). However, the activity of these compounds is not alwaysentirely satisfactory under certain circumstances, in particular whenlow concentrations of active compound and low application rates areused.

New N-pyrazolylanilines and N-pyrazolylaminopyridines of the formula (I)##STR2## have now been found, in which X represents C--NO₂, C-halogen,C-halogenoalkyl or N,

Y represents NO₂, CN, halogen or halogenoalkyl,

Z represents NO₂, halogen, halogenoalkyl, halogenoalkoxy orhalogenoalkylthio,

R¹ represents hydrogen, or in each case optionally substituted alkyl,alkenyl, alkinyl, aryl, hetaryl or aralkyl,

R² and R³ independently of one another represent hydrogen, halogen,cyano or nitro, or in each case optionally substituted alkyl, aryl orhetaryl, or one of the radicals CO₂ R⁵, CONR⁶ R⁷, CSNR⁶ R⁷, S(O)_(n) R⁸,

R⁴ represents halogen, in each case optionally substituted alkyl,alkenyl, alkinyl, aralkyl, aryloxy or aralkyloxy or one of the radicalsSO₂ NR⁶ R⁷, SO₂ R⁹, COR¹⁰ or CH₂ N(R⁹)_(w), in which

w represents CO₂ R⁵ or SO₂ R⁵,

R⁵ represents alkyl,

R⁶ and R⁷ independently of one another represent hydrogen or alkyl, ortogether with the N atom to which they are bonded form a ring whichoptionally contains at least one further hetero atom,

R⁸ represents alkyl or halogenoalkyl,

R⁹ represents alkyl or optionally substituted aryl,

R¹⁰ represents alkyl, alkoxy, or in each case optionally substitutedaryl or aryloxy, and

n represents 0, 1 or 2,

with the proviso that

R¹ does not represent alkyl, optionally substituted phenyl, optionallysubstituted phenylsulfonyl or pyridyl and/or

R² does not represent hydrogen, alkyl or phenyl and/or

R³ does not represent hydrogen, CN, halogen, optionally substitutedphenyl, optionally substituted phenylsulfonyl, CO₂ -alkyl or CO₂-benzyl,

if

R⁴ represents hydrogen and simultaneously

X represents C--NO₂ and simultaneously one of the substituents

Y or Z represents halogenoalkyl and the other substituent representsNO₂.

Furthermore, it has been found that A) the N-pyrazolylanilines andN-pyrazolylaminopyridines of the formula (I) are obtained by a processwhich comprises reacting 5-aminopyrazoles of the formula (II) ##STR3##in which R¹, R² and R³ have the abovementioned meanings with compoundsof the formula (III) ##STR4## in which Hal represents fluorine,chlorine, bromine or iodine, preferably fluorine or chlorine, and

X, Y and Z have the abovementioned meaning in the presence of a base andin the presence of a diluent, and, if appropriate, subsequently reactingthe resulting compounds of the formula (Ia) ##STR5## in which X, Y, Z,R¹, R² and R³ have the abovementioned meanings with compounds of theformula (IV)

    R.sup.11 --V                                               (IV)

in which

V represents an anionic leaving group such as, for example, chlorine,bromine, iodine, acetoxy, tosyl or mesyl and

R¹¹ has the meaning mentioned above for R⁴ with the exception ofhydrogen in the presence of a base and if appropriate in the presence ofa diluent, and that B) compounds of the formula (Ib) ##STR6## in whichR¹, R², R³, X, Y and Z have the abovementioned meanings and

R¹¹ has the abovementioned meaning are obtained by a process whichcomprises reacting 5-aminopyrazoles of the formula (II) ##STR7## inwhich R¹, R² and R³ have the abovementioned meanings with compounds ofthe formula (IV)

    R.sup.11 --V                                               (IV)

in which

R¹¹ and V have the abovementioned meanings in the presence of a base andin the presence of a diluent, and subsequently reacting the resultingcompounds of the formula (V) ##STR8## in which R¹, R², R³ and R¹¹ havethe abovementioned meanings with compounds of the formula (III) ##STR9##in which Hal, X, Y and Z have the abovementioned meanings in thepresence of a base and in the presence of a diluent.

The new compounds of the formula (I) have properties which allow them tobe used as pesticides. In particular, they can be used as insecticides,arthropodicides and fungicides.

Formula (I) provides a general definition of the N-pyrazolylanilines andN-pyrazolylaminopyridines according to the invention.

Preferred substituents or ranges of the radicals listed in the formulaementioned hereinabove and hereinbelow will be illustrated in thefollowing text.

X preferably represents C--NO₂, C-halogen, C--C₁ -C₆ -halogenoalkyl orN.

Y preferably represents NO₂, CN, halogen or C₁ -C₆ -halogenoalkyl.

Z preferably represents NO₂, halogen, C₁ -C₆ -halogenoalkyl, C₁ -C₆-halogenoalkoxy or C₁ -C₆ -halogenoalkylthio.

R¹ preferably represents hydrogen, C₁ -C₈ -alkyl, C₁ -C₈ -cyanoalkyl, C₁-C₈ -halogenoalkyl, C₁ -C₈ -hydroxyalkyl, C₁ -C₄ -alkoxy-C₁ -C₈ -alkyl,or represents phenyl, benzyl or phenethyl, each of which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of halogen, C₁ -C₄ -alkyl, C₁ -C₄-halogenoalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -halogenoalkylthio, phenyl, phenoxy, CN or NO₂, orrepresents pyridyl which is monosubstituted to trisubstituted byidentical or different substituents from the series consisting ofhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkyl, orrepresents pyrimidyl, thiadiazolyl or thiazolyl, each of which isoptionally monosubstituted or disubstituted by identical or differentsubstituents from the series consisting of halogen, C₁ -C₄ -alkyl, C₁-C₄ -alkoxy or C₁ -C₄ -halogenoalkyl.

R² and R³ independently of one another preferably represent hydrogen,halogen, cyano, nitro, C₁ -C₈ -alkyl, C₁ -C₈ -halogenoalkyl, C₁ -C₈-hydroxyalkyl, C₁ -C₄ -alkoxy-C ₁ -C₈ -alkyl, or represent phenyl orthienyl, each of which is optionally monosubstituted to trisubstitutedby identical or different substituents from the series consisting ofhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkyl or C₁ -C₄-halogenoalkylthio, or represent one of the radicals CO₂ R⁵, CONR⁶ R⁷,CSNR⁶ R⁷, S(O)_(n) R⁸.

R⁴ represents hydrogen, C₁ -C₈ -alkyl, C₁ -C₈ -halogenoalkyl, C₁ -C₈-hydroxyalkyl, C₁ -C₄ -alkoxy-C₁ -C₈ -alkyl, C₃ -C₈ -alkenyl, C₃ -C₈-halogenoalkenyl, C₃ -C₈ -hydroxyalkenyl, C₁ -C₄ -alkoxy-C₃ -C₈-alkenyl, C₃ -C₈ -alkinyl, C₃ -C₈ -halogenoalkinyl, C₃ -C₈-hydroxyalkinyl, C₁ -C₄ -alkoxy-C₃ -C₈ -alkinyl, or represents phenoxy,benzyl or benzyloxy, each of which is optionally monosubstituted totrisubstituted by identical or different substituents from the seriesconsisting of halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkyl or C₁ -C₄ -halogenoalkoxy, or represents one of theradicals SO₂ R⁹, COR¹⁰, CH₂ --N(R⁹)w, SO₂ NR⁶ R⁷.

w preferably represents CO₂ R⁵ or SO₂ R⁵.

R⁵ preferably represents C₁ -C₈ -alkyl.

R⁶ and R⁷ independently of one another preferably represent hydrogen, C₁-C₈ -alkyl, or together with the N atom to which they are bonded are 5-to 7-membered ring which optionally contains up to two additional heteroatoms from the series consisting of N, O and S.

R⁸ preferably represents C₁ -C₈ -alkyl or C₁ -C₈ -halogenoalkyl.

R⁹ preferably represents C₁ -C₈ -alkyl, or represents phenyl which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents from the series consisting of halogen, C₁ -C₄ -alkyl or C₁-C₄ -alkoxy.

R¹⁰ preferably represents C₁ -C₈ -alkyl or C₁ -C₈ -alkoxy, or representsphenyl or phenoxy, each of which is optionally monosubstituted totrisubstituted by halogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy.

n preferably represents 0, 1 or 2.

X particularly preferably represents C--NO₂, C-fluoro, C-chloro,C-bromo, C₁ -C₃ -halogenoalkyl having 1 to 5 identical or differenthalogen atoms from the series consisting of fluorine, chlorine andbromine, or represents N.

Y particularly preferably represents NO₂, CN, fluorine, chlorine,bromine or C₁ -C₄ -halogenoalkyl having 1 to 7 identical or differenthalogen atoms from the series consisting of fluorine, chlorine andbromine.

Z particularly preferably represents NO₂, fluorine, chlorine, bromine,C₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy or C₁ -C₄-halogenoalkylthio, each of which has 1 to 7 identical or differenthalogen atoms from the series consisting of fluorine, chlorine andbromine.

R¹ particularly preferably represents C₁ -C₆ -alkyl, C₁ -C₆ -cyanoalkyl,C₁ -C₆ -halogenoalkyl having one to three identical or different halogenatoms from the series consisting of fluorine, chlorine and bromine, orrepresents C₁ -C₆ -hydroxyalkyl, C₁ -C₂ -alkoxy-C₁ -C₆ -alkyl, orrepresents phenyl, benzyl or phenethyl, which in each case is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, C₁ -C₃-alkyl, C₁ -C₃ -alkoxy, C₁ -C₃ -halogenoalkyl, C₁ -C₃ -halogenoalkoxy orC₁ -C₄ -halogenoalkylthio, each of which has one to three identical ordifferent halogen atoms from the series consisting of fluorine, chlorineand bromine, or CN or nitro, or represents pyridyl which ismonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, C₁ -C₃-alkyl, C₁ -C₃ -alkoxy or C₁ -C₃ -halogenoalkyl having one to threeidentical or different halogen atoms from the series consisting offluorine, chlorine and bromine, or represents pyrimidyl or thiadiazolyl,each of which is optionally monosubstituted or disubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, C₁ -C₃ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃-halogenoalkyl having one to three identical or different halogen atomsfrom the series consisting of fluorine, chlorine and bromine.

R² and R³ independently of one another particularly preferably representhydrogen, fluorine, chlorine, bromine, CN, C₁ -C₆ -alkyl, C₁ -C₆-halogenoalkyl having one to six identical or different halogen atomsfrom the series consisting of fluorine, chlorine and bromine, orrepresent C₁ -C₂ -alkoxy-C₁ -C₆ -alkyl, or represent phenyl or thienyl,each of which is optionally monosubstituted to trisubstituted byidentical or different substituents from the series consisting offluorine, chlorine, bromine, C₁ -C₃ -alkyl or C₁ -C₃ -alkoxy, orrepresent one of the radicals CO₂ R⁵, CONR⁶ R⁷, CSNR⁶ R⁷, S(O)_(n) R⁸.

R⁴ particularly preferably represents hydrogen, or represents C₁ -C₆-alkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionallysubstituted by one to three halogen atoms from the series consisting offluorine, chlorine and bromine, or represents C₁ -C₄ -alkoxymethyl, orrepresents benzyl or benzyloxy, each of which is optionallymonosubstituted or disubstituted by fluorine, chlorine or bromine, orrepresents one of the radicals SO₂ R⁹, COR¹⁰, CH₂ --N(R⁹)CO₂ R⁵.

R⁵ particularly preferably represents C₁ -C₄ -alkyl.

R⁶ and R⁷ independently of one another particularly preferably representhydrogen, methyl or ethyl.

R⁸ particularly preferably represents C₁ -C₄ -alkyl or C₁ -C₄-halogenoalkyl having one to three fluorine and/or chlorine atoms.

R⁹ particularly preferably represents C₁ -C₄ -alkyl, or representsphenyl which is optionally monosubstituted to trisubstituted byfluorine, chlorine and/or bromine.

R¹⁰ particularly preferably represents C₁ -C₄ -alkyl, or representsphenyl which is optionally monosubstituted to trisubstituted byfluorine, chlorine and/or bromine.

n particularly preferably represents 0, 1 or 2.

X very particularly preferably represents C--NO₂, C--Cl or N.

Y very particularly preferably represents N₂, CN, fluorine, chlorine orCF₃.

Z very particularly preferably represents NO₂, fluorine, chlorine, CF₃,OCF₃ or SCF₃.

R¹ very particularly preferably represents methyl, ethyl, n- ori-propyl, n-butyl, i-butyl, s-butyl, t-butyl, the isomeric pentyls orisomeric hexyls, each of which is optionally monosubstituted totrisubstituted by fluorine and/or chlorine or monosubstituted by cyanoor represents phenyl, benzyl or phenethyl each of which is optionallymonosubstituted to trisubstituted by identical or different substituentsfrom the series consisting of fluorine, chlorine, bromine, CF₃, OCF₃,SCF₃, CN and NO₂, or represents pyridyl, pyrimidyl or thiadiazolyl, eachof which is optionally monosubstituted to trisubstituted by identical ordifferent substituents from the series consisting of fluorine, chlorine,bromine or CF₃.

R² and R³ independently of one another very particularly preferablyrepresent hydrogen, chlorine, bromine, CN, methyl, ethyl, n-propyl,i-propyl, n-butyl, t-butyl, CF₃, C₂ F₅ or CH₂ OCH₃, or represent phenylwhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents from the series consisting of fluorine, chlorine,bromine, methyl and methoxy, or represent one of the radicals CO₂ R⁵,CONR⁶ R⁷ or S(O)_(n) R⁸.

R⁴ very particularly preferably represents hydrogen, methyl, ethyl,2-propenyl, 2-propinyl, methoxymethyl, ethoxymethyl, propoxymethyl,i-propoxymethyl or n-butoxymethyl.

R⁵ very particularly preferably represents methyl or ethyl.

R⁶ and R⁷ very particularly preferably represent hydrogen.

R⁸ very particularly preferably represents methyl, ethyl,trifluoromethyl, 1,1-difluoroethyl or 2,2,2-trifluoroethyl.

n very particularly preferably represents 0, 1 or 2.

The following applies in each case:

R¹ does not represent alkyl, optionally substituted phenyl, optionallysubstituted phenylsulfonyl or pyridyl and/or

R² does not represent hydrogen, alkyl or phenyl and/or

R³ does not represent hydrogen, CN, halogen, optionally substitutedphenyl, optionally substituted phenylsulfonyl, CO₂ -alkyl or CO₂-benzyl,

if

R⁴ represents hydrogen and simultaneously

X represents C--NO₂ and simultaneously one of the substituents

Y or Z represents halogenoalkyl and the other substituent representsNO₂.

A preferred group of compounds are compounds of the formula (I-1)##STR10## in which R¹, R², R³, R⁴, X, Y and Z have the above mentionedmeanings,

with the proviso that

R¹ does not represent alkyl, optionally substituted phenyl, optionallysubstituted phenylsulfonyl or pyridyl and/or

R² does not represent hydrogen, alkyl or phenyl and/or

R³ does not represent hydrogen, CN, halogen, optionally substitutedphenyl, optionally substituted phenylsulphonyl, CO₂ -alkyl or CO₂-benzyl,

if

R⁴ represents hydrogen or simultaneously

X represents C--NO₂ and simultaneously one of the substituents

Y or Z represents halogenoalkyl and the other substituent representsNO₂.

A particularly preferred group of compounds are compounds of the formula(I-2) ##STR11## in which X¹ has the above mentioned meanings given forXwith the exception of C--NO₂ and

R¹, R², R³, R⁴, Y and Z have the above mentioned meanings,

with the proviso that

Y does not represent NO₂ if Z represents NO₂.

A very particularly preferred group of compounds are compounds of theformula (I-3) ##STR12## in which X¹ has the above mentioned meaning,

Y¹ has the above mentioned meanings given for Y with the exception ofNO₂ and

R¹, R², R³, R⁴ and Z have the above mentioned meanings.

The definitions of radicals or illustrations mentioned above in generalor in preferred ranges can be combined as desired with each other, thatis to say combinations between each of the ranges and preferred rangesare also possible. They apply to the end products and analogously to theprecursors and intermediates.

Compounds of the formula (I), (I-1), (I-2) and (I-3) which are preferredaccording to the invention are those which in each case contain acombination of the meanings listed above as being preferred(preferable).

Compounds of the formula (I), (I-1), (I-2) and (I-3) which areparticularly preferred according to the invention are those which ineach case contain a combination of the meanings listed above as beingparticularly preferred.

Compounds of the formula (I), (I-1), (I-2) and (I-3) which are veryparticularly preferred according to the invention are those which ineach case contain a combination of the meanings listed above as beingvery particularly preferred.

The hydrocarbon radicals such as alkyl which have been mentioned abovein the definition of the compounds according to the invention are, asfar as this is possible, in each case straight-chain or branched, alsoin connection with hetero atoms, such as alkoxy.

If, for example, 1-methyl-3-thiomethyl-4-cyano-5-aminopyrazole,1-chloro-2,6-dinitro-4-trifluoromethylbenzene and chloromethyl ethylether are used as starting substances, the course of the reaction ofprocess A) according to the invention can be represented by thefollowing equation: ##STR13## if, for example,1-methyl-3-pentafluoroethyl-4-trifluoromethyl-5-aminopyrazole,iodomethane and 2-chloro-4-trifluoromethyl-2,6-dinitrobenzene are usedas starting substances, the course of the reaction of process B)according to the invention can be represented by the following equation:##STR14##

The 5-aminopyrazoles of the formula (II) required as starting substancesfor carrying out the process according to the invention are known and/orcan be prepared by known processes (cf., for example, Chem. Het. Comp.17 (1981), 1; J. Org. Chem. 21 (1956), 1240; EP 0 201 852; EP 0 392 241;Chem. Ber. 95 (1962), 2871; J. Org. Chem. 29 (1964) 1915; Isv. Attad.Nauk SSR, Ser. Khim 11 (1990) 2583; J. Chem. Research (5), 1993, 76).

The compounds of the formula (III) which are required as startingsubstances for carrying out the process according to the invention areknown and/or can be prepared by known methods (cf., for example, EP 0398 499, J. Org. Chem. 47 (1982) 2856; U.S. Pat. No. 3,888,932; U.S.Pat. No. 3,928,416).

The compounds of the formula (IV) which are required as startingsubstances for carrying out the process according to the invention areknown substances of organic chemistry.

The following information on the process according to the inventionapplies in each case to both steps of Preparation Alternatives A) andB).

The process according to the invention for the preparation of the newcompounds of the formula (I) is preferably carried out using diluents.Suitable diluents are virtually all inert organic solvents. Thesepreferably include aliphatic and aromatic, optionally halogenatedhydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleumether, benzine, ligroin, benzene, toluene, xylene, methylene chloride,ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, ethers such as diethyl ether and dibutyl ether,glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran anddioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropylketone and methyl isobutyl ketone, esters such as methyl acetate andethyl acetate, nitriles such as, for example, acetonitrile andpropionitrile, amides such as, for example, dimethylformamide,dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulfoxide,tetramethylene sulfone and hexamethylphosphoric triamide.

Bases which can be employed in the process according to the inventionare all acid-binding agents which can conventionally be used forreactions of this type. The following are preferably suitable: alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal hydroxides and alkaline earth metal hydroxides, such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal carbonates, alkali metal hydrogen carbonates, alkalineearth metal carbonates and alkaline earth metal hydrogen carbonates,such as sodium carbonate, sodium hydrogen carbonate, potassium carbonateor potassium hydrogen carbonate and also calcium carbonate, alkali metalacetates, such as sodium acetate and potassium acetate, alkali metalalcoholates, such as sodium tert-butylate and potassium tert-butylate,furthermore basic nitrogen compounds, such as trimethylamine,triethylamine, tripropylamine, tributylamine, diisobutylamine,dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine,N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-,3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl-and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo 4,3,0!-non-5-ene (DBN),1,8-diazabicyclo- 5,4,0!-undec-7-ene (DBU) and 1,4-diazabicyclo2,2,2!-octane (DABCO).

The reaction temperatures in the process according to the invention canbe varied within a substantial range. In general, the process is carriedout at temperatures between 0° C. and 100° C., preferably attemperatures between 10° C. and 80° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it can also be carried out under elevatedor reduced pressure.

To carry out the process according to the invention, the startingsubstances required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use one of the twocomponents employed in each case in a larger excess. In general, thereactions are carried out in a suitable diluent in the presence of anacid acceptor, and the reaction mixture is stirred for several hours atthe temperature required in each case. Working-up in the processaccording to the invention is carried out in each case by customarymethods (cf. Preparation Examples).

The compounds of the formula (I) according to the invention can beemployed as pesticides. Pests are undesired animal pests, in particularinsects and mites, which are harmful to plants or higher animals.

The active compounds according to the invention are suitable forcombating animal pests, preferably arthropods, in particular insects andarachnids, encountered in agriculture, in forestry, in the protection ofstored products and of materials, and in the hygiene field, and havegood plant tolerance and favorable toxicity to warm-blooded animals.They are active against normally sensitive and resistant species andagainst all or some stages of development. The abovementioned pestsinclude:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, Pediculus humanus corporis, Haematopinusspp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Phylloxera vastatrix, Pemphigusspp., Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps,Lecaniuh corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. andPsylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flanmmea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus Latrodectusmactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychu spp.,Hemitarsonemus spp.

The active compounds according to the invention also have a fungicidalactivity and can be employed as fungicides in plant protection, forexample against the causative organism of rice blast disease(Pyricularia oryzae).

Fungicidal agents are employed in plant protection for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Some causative organisms of fungal diseases which come under the genericnames listed above may be mentioned as examples, but not by way oflimitation:

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, synonym: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, synonym: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

In this context, the active compounds according to the invention can beemployed with particular success for combating diseases in fruit andvegetable growing such as, for example, against the causative organismof apple scab (Venturia inaequalis). Besides, the active compoundsaccording to the invention have a good in-vitro activity.

For use as insecticides, acaricides and fungicides the active compoundsaccording to the invention can be present in their commerciallyavailable formulations and in the use forms, prepared from theseformulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphates, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas, substances produced by microorganisms and thelike.

The following may be mentioned as insecticides:

acrinathrin, alphamethrin, betacyfluthrin, bifenthrin, brofenprox,cis-resmethrin, clocythrin, cycloprothin, cyfluthrin, cyhalothrin,cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, fluvalinate, lambda-cyhalothrin, permethrin,pyresmethrin, pyrethrum, silafluofen, tralomethrin, zetamethrin,

Alanycarb, bendiocarb, benfuracarb, bufencarb, butocarboxim, carbaryl,cartap, ethiofencarb, fenobucarb, fenoxycarb, isoprocarb, methiocarb,methomyl, metolcarb, oxamyl, pirimicarb, promecasrb, propoxur, terbam,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, acephate, azinphosA, azinphos M, bromophos A, cadusafos, carbophenothion, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos M, cyanophos, demeton M,demeton-S-methyl, demeton S, diazinon, dichlorvos, dicliphos,dichlofenthion, dicrotophos, dimethoate, dimethylvinphos, dioxathion,disulfoton, edifenphos, ethion, etrimphos, fenitrothion, fenthion,fonophos, formothion, heptenophos, iprobenfos, isazophos, isoxathion,phorate, malathion, mecarbam, mevinphos, mesulfenphos, methacrifos,methamidophos, methidathion, monocrotophos, naled, omethoate,oxydemethon M, oxydeprofos, parathion A, parathion M, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos A,pirimiphos M, propaphos, prothiophos, prothoate, pyraclophos,pyridaphention, quinalphos, salithion, sebufos, sulfotep, sulprofos,tetrachlorvinphos, temephos, thiomethon, thionazin, trichlorfon,triazophos, vamidothion,

buprofezin, lufenuron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, pyriproxifen, tebufenozide, teflubenzuron,triflumuron,

imidacloprid, nitenpyram,

abamectin, amitraz, avermectin, azadirachtin, bensultap, Bacillusthuringiensis, cyromazine, diafenthiuron, emamectin, ethofenprox,fenpyrad, fipronil, flufenprox, lufenuron, metaldehyde, milbemectin,pymetrozine, tebufenpyrad, triazuron,

aldicarb, bendiocarb, benfuracarb, carbofuran, carbosulfan,chlorethoxyfos, cloethocarb, disulfoton, ethoprophos, etrimphos,fenamiphos, fipronil, fonofos, fosthiazate, furathiocarb, HCH,isazophos, isofenphos, methiocarb, monocrotophos, nitenpyram, oxamyl,phorate, phoxim, prothiofos, pyrachlofos, sebufos, silafluofen,tebupirimphos, tefluthrin, terbufos, thiodicarb, thiafenox,

azocyclotin, butylpyridaben, clofentezine, cyhexatin, diafenthiuron,diethion, emamectin, fenazaquin, fenbutatin oxide, fenthiocarb,fenpropathrin, fenpyrad, fenpyroximate, fluazinam, fluazuron,flucycloxuron, flufenoxuron, fluvalinate, fubfenprox, hexythiazox,ivemectin, methidathion, monocrotophos, moxidectin, phosalone,profenofos, pyraclofos, pyridaben, pyrimidifen, tebufenpyrad,thuringiensin, triarathene, triazophos,

the compound of the formula ##STR15## and the compound of the formula##STR16##

The following may be mentioned as fungicides:

sulfenamides, such as dichlorofluanide (Euparen), tolylfluanide(Methyleuparen), folpet, fluorofolpet;

benzimidazoles, such as carbendazim (MBC), benomyl, fuberidazole,thiabendazole or their salts;

thiocyanates such as thiocyanatomethylthiobenzothiazole (TCMTB),methylene bisthiocyanate (MBT);

quaternary ammonium compounds, such as benzyldimethyltetradecylammoniumchloride, benzyl-dimethyl-dodecylammonium chloride, dodecyl-dimethylammonium chloride;

morpholine derivatives, such as C₁₁ -C₁₄-4-alkyl-2,6-dimethyl-morpholine homologs (tridemorph), (±)-cis-4-tert-butylphenyl)-2-methylpropyl!-2,6-dimethylmorpholine(fenpropimorph), falimorph;

phenols, such as o-phenylphenol, tribromophenol, tetrachlorophenol,pentachlorophenol, 3-methyl-4-chlorophenol, dichlorophene, chloropheneor their salts;

azoles, such as triadimefon, triadimenol, bitertanol, tebuconazole,propiconazole, azaconazole, hexaconazole, prochloraz, cyproconazole,1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-(1,2,4-triazol-1-yl)-propan-2-olor1-(2-chlorophenyl)-2-(1,2,4-triazol-1-yl-methyl)-3,3-dimethyl-butan-2-ol;

iodopropargyl derivatives such as iodopropargyl butylcarbamate (IPBC),iodopropargyl chlorophenyl formal, iodopropargyl phenylcarbamate,iodopropargyl hexylcarbamate, iodopropargyl cyclohexylcarbamate,iodopropargyloxyethyl phenylcarbamate;

iodine derivatives such as diiodomethyl-p-aryl sulfones, for examplediiodomethyl-p-tolyl sulfone;

bromine derivatives such as bromopol;

isothiazolines such as N-methylisothiazolin-3-one,5-chloro-N-methylisothiazolin-3-one,4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one(octilinone);

benzoisothiazolinones, cyclopenteneisothiazolines;

pyridines, such as 1-hydroxy-2-pyridinethione (and their sodium, iron,manganese or zinc salts), tetrachloro-4-methylsulfonylpyridine;

metal soaps, such as tin naphthenate, tin octoate, tin 2-ethylhexanoate,tin oleate, tin phosphate, tin benzoate, copper naphthenate, copperoctoate, copper 2-ethylhexanoate, copper oleate, copper phosphate,copper benzoate, zinc naphthenate, zinc octoate, zinc 2-ethylhexanoate,zinc oleate, zinc phosphate, zinc benzoate, oxides, such as TBTO, Cu₂ O,CuO, ZnO;

organotin compounds, such as tributyltin naphthenate and tributyltinoxide;

dialkyldithiocarbamates, such as sodium and zinc salts ofdialkyldithiocarbamates, tetramethylthiuram disulfide (TMTD);

nitrites such as 2,4,5,6-tetrachloroisophthalonitrile (chlorthalonil)and other microbicides having an activated halogen group, such as Cl-Ac,MCA, tectamer, bromopol, bromidox;

benzothiazoles, such as 2-mercaptobenzothiazoles; dazomet;

quinolines, such as 8-hydroxyquinoline;

formaldehyde-releasing compounds, such as benzyl alcoholmono(poly)hemiformal, oxazolidines, hexahydro-s-triazines,N-methylchloroacetamide;

tris-N-(cyclohexyldiazeniumdioxy)-aluminum,N-(cyclohexyldiazeniumdioxy)-tributyltin or K salts,bis-(N-cyclohexyl)diazenium-(dioxy-copper or -aluminum).

The active compounds according to the invention can also be present intheir commercially available formulations and in the use forms preparedfrom these formulations in a mixture with synergists. Synergists arecompounds by means of which the action of the active compounds isincreased without the synergist added having to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

The compounds according to the invention are also specially suitable forthe treatment of vegetative and generative propagation material such as,for example, seeds of cereals, maize, vegetables and the like, or ofbulbs, cuttings and the like.

When used against hygiene pests and pests of stored products, the activecompounds are distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

The active compounds can be employed as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are applied in the customary manner, for example bypouring, spraying, atomizing, scattering.

The active compound according to the invention can be applied before orafter emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound applied can vary within wide limits. Itdepends essentially on the nature of the desired effect. In general,application rates are between 10 g and 10 kg of active compound perhectare of soil surface, preferably between 50 g and 5 kg per ha.

To prepare the pesticides, the active compounds according to theinvention, depending on their particular physical and/or chemicalproperties, can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, natural and synthetic materials impregnated with activecompound, very fine capsules in polymeric substances and in coatingcompositions for seed, and formulations used with burning equipment,such as fumigating cartridges, fumigating cans, fumigating coils and thelike, as well as ULV cold mist and warm mist formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulfoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example ligninsulfite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention are not only activeagainst plant, hygiene and stored product pests, but also, in theveterinary medicine sector, against animal ectoparasites such as scalyticks, argasidae, scab mites, trombidae, flies (stinging and sucking),parasitic fly larvae, lice, hair lice, bird lice and fleas. For example,they have an outstanding activity against ticks such as, for example,Boophilus microplus.

The active compounds of the formula (I) according to the invention arealso suitable for the combating of arthropods which infest usefulanimals in agriculture such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks,geese, bees, other domestic animals such as, for example, dogs, cats,cage birds, aquarium fish and so-called experimental animals such as,for example, hamsters, guinea pigs, rats and mice. The aim of combatingthese arthropods is to reduce fatalities and reductions in yield (inmeat, milk, wool, skins, eggs, honey, etc.) so that the use of theactive compound according to the invention renders the keeping ofanimals more economic and more simple.

In the veterinary sector the active compounds according to the inventionare employed in a known manner by enteral administration in the form of,for example, tablets, capsules, potions, drenches, granules, pastes,boli, by the feed-through method, suppositories, by parenteraladministration, for example by injection (intramuscular, subcutaneous,intravenous, intraperitoneal etc.), by implants, by nasaladministration, by dermal application in the form, for example, ofdipping or bathing, spraying, pouring on and spotting on, washing,dusting and with the aid of shaped articles which contain activecompound, such as neck bands, ear tags, tail tags, limb bands, halters,marking devices and the like.

The compositions according to the invention, besides at least onecompound of the general formula (I) and, if appropriate, besidesextenders and auxiliaries, preferably comprise at least one surfactant.

Unless otherwise specified, all percentages are by weight.

The preparation of the compounds of the formula (I) according to theinvention will be illustrated by the Preparation Examples which follow.

PREPARATION EXAMPLES Example 1 ##STR17## 1.2 g (0.04 mol) of NaH (80%dispersion in mineral oil) are introduced into 20 ml of DMF, and asolution of 5.3 g (0.02 mol) of1-(4-chlorophenyl)-3-thiomethyl-4-cyano-5-aminopyrazole is added. 5.0 g(0.02 mol) of 3,4,5-tri-chlorobenzotrifluoride are added, and themixture is heated for 18 hours at 80° C. The reaction mixture is pouredinto 300 ml of ice-water to which 10 ml of glacial acetic acid have beenadded and this mixture is subseqently extracted using dichloromethane(3×100 ml). The combined organic phases are dried, the solvent isremoved under reduced pressure, and the residue is chromatographed onsilica gel using dichloromethane as the eluent. 4.5 g (47% of theory) ofN-1-(4-chlorophenyl)-3-thiomethyl-4-cyanopyrazol-5-yl!-2,6-dichloro-4-trifluoromethylanilineare obtained.

M.p.: 135° C.

Example 2 ##STR18## 1.14 g (0.038 mol) of NaH (80% dispersion in mineraloil) are introduced into 100 ml of THF and 6.0 g (0.019 mol) of1-(4-chlorophenyl)-3-thiomethyl-4-cyano-5-aminopyrazole are added inportions. 4.3 g (0.020 mol) of 2,3-dichloro-5-trifluoromethylpyridineare subsequently added dropwise, and the mixture is refluxed for 18hours. The reaction mixture is cooled and poured into 300 ml ofice-water to which 10 ml of glacial acetic acid have been added, and theyellow precipitate is filtered off with suction. 6.5 g (75% of theory)of N-1-(4-chlorophenyl)-3-thiomethyl-4-cyanopyrazol-5-yl!-2-amino-3-chloro-5-trifluoromethylpyridineare obtained.

M.p.: 194° C.

Example 3 ##STR19## 0.35 g (0.0116 mol) of NaH (80% dispersion inmineral oil) is introduced into 50 ml of THF, and 3.0 g (0.0058 mol) ofN-(1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl)-2,6-dinitro-4-trifluoromethylaniline in 10 ml of THF and 1.1 g (0.0116mol) of chloromethyl ethyl ether are added in succession. The reactionmixture is refluxed for 2 hours, cooled and poured into 400 ml ofice-water. The precipitate which has separated out is filtered off withsuction and dried. 2.9 g (86% of theory) ofN-ethoxymethyl-N-(1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl)-2,6-dinitro-4-trifluoromethylanilineis obtained.

M.p.: 103° C.

The following compounds of the formula (I-1) are obtained analogouslyand in accordance with the general information instructions:

                                      TABLE 1                                     __________________________________________________________________________     ##STR20##                                                                    Ex. No.                                                                            R.sup.1      R.sup.2   R.sup.3                                                                             R.sup.4  X     Y   Z   M.p.                 __________________________________________________________________________                                                             (°C.)         4    C.sub.6 H.sub.5 *                                                                          SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          163                  5    C.sub.6 H.sub.5                                                                            SCH.sub.3 CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          80                   6    C.sub.6 H.sub.5                                                                            SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          120                  7    C.sub.6 H.sub.5                                                                            SCH.sub.3 CN    H        CCl   CN  CF.sub.3                                                                          122                  8    C.sub.6 H.sub.5                                                                            SCH.sub.3 CN    H        CCl   F   CF.sub.3                                                                          Resin                9    C.sub.6 H.sub.5                                                                            SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          83                   10                                                                                  ##STR21##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          212                  11                                                                                  ##STR22##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          135                  12                                                                                  ##STR23##   SCH.sub.3 CN    H        CCl   CN  CF.sub.3                                                                          157                  13                                                                                  ##STR24##   SCH.sub.3 CN    H        CCl   F   CF.sub.3                                                                          152                  14                                                                                  ##STR25##   SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          194                  15                                                                                  ##STR26##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          220                  16                                                                                  ##STR27##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          165                  17                                                                                  ##STR28##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          188                  18                                                                                  ##STR29##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          163                  19                                                                                  ##STR30##   SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          172                  20                                                                                  ##STR31##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          160                  21                                                                                  ##STR32##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          157                  22                                                                                  ##STR33##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          62                   23                                                                                  ##STR34##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          128                  24                                                                                  ##STR35##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          Oil                  25                                                                                  ##STR36##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          90                   26                                                                                  ##STR37##   SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          215                  27                                                                                  ##STR38##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          270                  28                                                                                  ##STR39##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          65                   29                                                                                  ##STR40##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          190                  30                                                                                  ##STR41##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          165                  31                                                                                  ##STR42##   SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          105                  32                                                                                  ##STR43##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          178                  33                                                                                  ##STR44##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          212                  34                                                                                  ##STR45##   SCH.sub.3 CN    H        N     Cl  CF.sub.3                                                                          173                  35   CH.sub.3     SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          150                  36   n-C.sub.3 H.sub.7                                                                          SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          149                  37   tBu          SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF3 150/                                                                          dec.                 38                                                                                  ##STR46##   SCH.sub.3 CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          112                  39   C.sub.6 H.sub.5                                                                            SOCH.sub.3                                                                              CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          92                   40   C.sub.6 H.sub.5                                                                            SO.sub.2 CH.sub.3                                                                       CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          172                  41   C.sub.6 H.sub.5                                                                            SCH.sub.3 CONH.sub.2                                                                          H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          >240                 42   C.sub.6 H.sub.5                                                                            SCH.sub.3 CONH.sub.2                                                                          H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          198                  43   C.sub.6 H.sub.5                                                                            SCH.sub.3 CONH.sub.2                                                                          H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          112                  44                                                                                  ##STR47##   H         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          130                  45                                                                                  ##STR48##   H         CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          150                  46                                                                                  ##STR49##   H         CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          188                  47                                                                                  ##STR50##   H         CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          170                  48                                                                                  ##STR51##   H         CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          200                  49                                                                                  ##STR52##   H         CN    H        CCl   Cl  CF.sub.3                                                                          173                  50                                                                                  ##STR53##   H         CN    H        N     Cl  CF.sub.3                                                                          148                  51   CH.sub.3     H         CONH.sub.2                                                                          H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          217                  52                                                                                  ##STR54##   H         CONH.sub.2                                                                          H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          200                  53                                                                                  ##STR55##   H         CO.sub.2 Et                                                                         H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          140                  54                                                                                  ##STR56##   SCH.sub.3 H     H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          137                  55                                                                                  ##STR57##   SOCH.sub.3                                                                              H     H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          230                  56                                                                                  ##STR58##   CN        H     H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          171                  57   CH.sub.3                                                                                    ##STR59##                                                                              H     H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          199                  58   CH.sub.3                                                                                    ##STR60##                                                                              H     H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          224                  59   CH.sub.3     CH.sub.3  CN    H        N     Cl  CF.sub.3                                                                          165                  60   CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          104                  61   CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          182                  62   CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CCl   Cl  CF.sub.3                                                                          84                   63   C.sub.6 H.sub.5                                                                            C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          120                  64   C.sub.6 H.sub.5                                                                            C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          89                   65                                                                                  ##STR61##   C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          Oil                  66                                                                                  ##STR62##   C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          106                  67                                                                                  ##STR63##   C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          60                   68                                                                                  ##STR64##   C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          126                  69   CH.sub.3     H         H     H        N     Cl  CF.sub.3                                                                          168                  70   C.sub.6 H.sub.5                                                                            H         H     H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          128                  71                                                                                  ##STR65##   CH.sub.3  SCF.sub.2 CH.sub.3                                                                  H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          169                  72                                                                                  ##STR66##   CH.sub.3  SCH.sub.2 CF.sub.3                                                                  H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          198                  73                                                                                  ##STR67##   CH.sub.2 OCH.sub.3                                                                      SCF.sub.3                                                                           H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          190                  74                                                                                  ##STR68##   CH.sub.2 OCH.sub.3                                                                      SCF.sub.2 CH.sub.3                                                                  H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          148                  75                                                                                  ##STR69##   CH.sub.3  SCF.sub.2 CH.sub.3                                                                  H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          76                   76   C.sub.6 H.sub.5                                                                            CN        CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          135                  77   C.sub.6 H.sub.5                                                                            CN        CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          96                   78                                                                                  ##STR70##   CN        CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          76                   79                                                                                  ##STR71##   CN        CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          103                  80                                                                                  ##STR72##   CN        CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          183                  81                                                                                  ##STR73##   CN        CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          102                  82                                                                                  ##STR74##   CF.sub.3  CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          68                   83                                                                                  ##STR75##   CF.sub.3  CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          78                   84                                                                                  ##STR76##   CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          129                  85                                                                                  ##STR77##   H         CF.sub.3                                                                            CH.sub.2 OEt                                                                           CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          198                  86   CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            CH.sub.2 OEt                                                                           CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                 87   C.sub.6 H.sub.5                                                                            C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            CH.sub.2 OEt                                                                           CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          90                   88                                                                                  ##STR78##   C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            CH.sub.2 OEt                                                                           CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          Oil                  89                                                                                  ##STR79##   H         CN    H        CCl   CN  CF.sub.3                                                                          Oil                  90   C.sub.6 H.sub.5                                                                            CN        CN    H        CCl   Cl  CF.sub.3                                                                          162                  91                                                                                  ##STR80##   CN        CN    H        CCl   Cl  CF.sub.3                                                                          110                  92                                                                                  ##STR81##   CN        CN    H        CCl   Cl  OCF.sub.3                93                                                                                  ##STR82##   CN        CN    H        CCl   Cl  CF.sub.3                 94                                                                                  ##STR83##   CN        CN    H        CCl   Cl  CF.sub.3                                                                          104                  95                                                                                  ##STR84##   CN        CN    H        CCl   Cl  CF.sub.3                                                                          182                  96   C.sub.6 H.sub.5                                                                            CF.sub.3  CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          Oil                  97   C.sub.6 H.sub.5                                                                            CF.sub.3  CN    H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                 98   C.sub.6 H.sub.5                                                                            CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          120                  99                                                                                  ##STR85##   CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 100                                                                                 ##STR86##   CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 101                                                                                 ##STR87##   CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 102                                                                                 ##STR88##   SO.sub.2 CH.sub.3                                                                       CN    H        CCl   Cl  CF.sub.3                                                                          87                   103                                                                                 ##STR89##   SOCH.sub.3                                                                              CN    H        CCl   Cl  CF.sub.3                                                                          71                   104                                                                                 ##STR90##   SCH.sub.3 CN    H        CCl   Cl  OCF.sub.3                105                                                                                 ##STR91##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          160                  106                                                                                 ##STR92##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          161                  107                                                                                 ##STR93##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                                                                          142                  108                                                                                 ##STR94##   CH.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          75                   109                                                                                 ##STR95##   H         CN    H        CCl   Cl  CF.sub.3                                                                          62                   110  CH.sub.3     SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                 111  tBu          SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                 112  CH.sub.3                                                                                    ##STR96##                                                                              CN    H        CCl   Cl  CF.sub.3                 113                                                                                 ##STR97##                                                                                  ##STR98##                                                                              CN    H        CCl   Cl  CF.sub.3                 114                                                                                 ##STR99##   SCH.sub.3 CN    H        CCl   Cl  CF.sub.3                 115                                                                                 ##STR100##  H         CN    H        CCl   Cl  CF.sub.3                 116                                                                                 ##STR101##  CN        CN    H        CCl   Cl  CF.sub.3                 117  CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            CH.sub.3 CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          Oil                  118  CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                             ##STR102##                                                                            CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                 119  CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                             ##STR103##                                                                            CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                 120  CH.sub.3     C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            SO.sub.2 N(CH.sub.3).sub.2                                                             CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                 121                                                                                 ##STR104##  C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          115                  122                                                                                 ##STR105##  C.sub.2 F.sub.5                                                                         CF.sub.3                                                                            H        CNO.sub.2                                                                           CF.sub.3                                                                          NO.sub.2                                                                          123                  123  tC.sub.4 H.sub.9                                                                           CN        CN    H        CCl   Cl  CF.sub.3                                                                          173                  124                                                                                 ##STR106##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          220                  125                                                                                 ##STR107##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          184                  126                                                                                 ##STR108##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          143                  127                                                                                 ##STR109##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          135                  128                                                                                 ##STR110##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          147                  129                                                                                 ##STR111##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          144                  130                                                                                 ##STR112##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          155                  131                                                                                 ##STR113##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          90                   132                                                                                 ##STR114##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          73                   133                                                                                 ##STR115##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          68                   134                                                                                 ##STR116##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          186                  135                                                                                 ##STR117##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          136                  136                                                                                 ##STR118##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          113                  137                                                                                 ##STR119##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          78                   138                                                                                 ##STR120##  CN        CN    H        CCl   Cl  CF.sub.3                                                                          76                   139                                                                                 ##STR121##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          84                   140                                                                                 ##STR122##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          148                  141                                                                                 ##STR123##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          103                  142                                                                                 ##STR124##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          88                   143                                                                                 ##STR125##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          103                  144                                                                                 ##STR126##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                                                                          67                   145  CH.sub.3     CH.sub.3  CN    H        CNO.sub.2                                                                           NO.sub.2                                                                          CF.sub.3                                                                          174                  146  tBu          CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 147                                                                                 ##STR127##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 148                                                                                 ##STR128##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 149                                                                                 ##STR129##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 150                                                                                 ##STR130##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 151                                                                                 ##STR131##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 152                                                                                 ##STR132##  CF.sub.3  CN    H        CCl   Cl  CF.sub.3                 153                                                                                 ##STR133##  C.sub.2 F.sub.5                                                                         CN    H        CCl   Cl  CF.sub.3                 154                                                                                 ##STR134##  CN        CN    H        CCl   Cl  CF.sub.3                 155                                                                                 ##STR135##  CN        CN    H        CCl   Cl  CF.sub.3                 156                                                                                 ##STR136##  CN        CN    H        CCl   Cl  CF.sub.3                 157                                                                                 ##STR137##  CN        CN    H        CCl   Cl  CF.sub.3                 158                                                                                 ##STR138##  CN        CN    H        CCl   Cl  CF.sub.3                 159  (CH.sub.2).sub.3 CH.sub.3                                                                  CN        CN    H        CCl   Cl  CF.sub.3                 160  (CH.sub.2).sub.2 OH                                                                        CN        CN    H        CCl   Cl  CF.sub.3                 161  CH.sub.2 CF.sub.3                                                                          CN        CN    H        CCl   Cl  CF.sub.3                 162  CH.sub.3     CN        CN    H        CCl   Cl  CF.sub.3                 163  C.sub.2 H.sub.5                                                                            CN        CN    H        CCl   Cl  CF.sub.3                 164  CH.sub.2 Ph  CN        CN    H        CCl   Cl  CF.sub.3                 __________________________________________________________________________     *C.sub.6 H.sub.5 = phenyl = Ph                                                Bu = butyl                                                                    Pr = propyl                                                                   Et = ethyl                                                               

Use Examples

In the use examples which follow, the compounds listed below wereemployed as comparison substances: ##STR139##

Example A

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), while theleaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the beetle larvae have been killed; 0% means thatnone of the beetle larvae have been killed.

In this test, a destruction rate of 100% was shown, after 3 days, forexample by the compounds of Preparation Examples 10, 11, 37, 44, 47, 60,71, 73 and 75 at an exemplary active compound concentration of 0.01%,while the prior-art compounds (A) and (B) resulted in no destruction.

Example B

Plutella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with caterpillars of the diamond-back moth (Plutellamaculipennis), while the leaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the caterpillars have been killed.

In this test, a destruction rate of at least 80% was shown, after 3days, for example by the compounds of Preparation Examples 13, 60, 61and 75 at an exemplary active compound concentration of 0.001%, whilethe prior-art compounds (A) and (B) resulted in no destruction.

Example C

Spodoptera test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with caterpillars of the fall armyworm (Spodoptera frugiperda),while the leaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the caterpillars have been killed.

In this test, a destruction rate of 100% was shown, after 3 days, forexample by the compounds of Preparation Examples 8, 11, 12, 13, 28, 30,31, 32, 60, 74 and 89 at an exemplary active compound concentration of0.1%, while the prior-art compound (A) resulted in no destruction.

Example D

Nephotettix test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with the green rice leafhopper (Nephotettix cincticeps) whilethe leaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the leafhoppers have been killed; 0% means that noneof the leafhoppers have been killed.

In this test, a destruction rate of 100% was shown, after 6 days, forexample by the compounds of Preparation Examples 22, 60 and 63 at anexemplary active compound concentration of 0.1%, while the prior-artcompounds (A) and (B) resulted in no destruction.

Example E

Tetranychus test (OP resistant)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentrations.

Bean plants (Phaseolus vulgaris) which are severely infested with alldevelopment stages of the greenhouse red spider mite (Tetranychusurticae) are dipped into a preparation of the active compound of thedesired concentration.

After the desired period of time, the effect in percent is determined.100% means that all the spider mites have been killed; 0% means thatnone of the spider mites have been killed.

In this test, a destruction rate of 100% was shown, after 7 days, forexample by the compounds of Preparation Examples 8, 13, 28 and 60 at anexemplary active compound concentration of 0.01%, while the prior-artcompound (A) resulted in no destruction.

Example F

Plasmopara test (vines)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Plasmopara viticola and then remain in a humidity chamberat 20 to 22° C. and 100% relative atmospheric humidity for 1 day. Theplants are then placed in a greenhouse at 21° C. and 90% atmospherichumidity for 5 days. The plants are then moistened and placed in ahumidity chamber for 1 day.

Evaluation is carried out 6 days after the inoculation.

In this test, a degree of effectiveness of at least 90% was shown, forexample, by the compounds of Preparation Examples 7, 16, 36, 37 and 60at an exemplary active compound concentration of 10 ppm.

Example G

Podosphaera test (apple)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated by dusting with conidiaof the causative organism of apple mildew (Podosphaera leucotricha).

The plants are then placed in a greenhouse at 23° C. and a relativeatmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation.

In this test, a degree of effectiveness of at least 96% was shown, forexample, by the compounds of Preparation Examples 44, 10, 37 and 60 atan exemplary active compound concentration of 25 ppm.

Example H

Venturia test (apple)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous conidiasuspension of the apple scab causative organism (Venturia inaequalis)and then remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at 20° C. and a relativeatmospheric humidity of about 70%.

Evaluation is carried out 12 days after the inoculation.

In this test, a degree of effectiveness of at least 99% was shown, forexample, by the compounds of Preparation Examples 37 and 60 at anexemplary active compound concentration of 10 ppm.

Example I

Test with Lucilia cuprina resistant larvae

Emulsifier: 35 parts by weight of ethylene glycol monomethyl ether

35 parts by weight of nonyl phenol polyglycol ether

To produce a suitable preparation of active compounds three parts byweight of active compound are mixed with seven parts by weight of theabove-mentioned solvent mixture and the concentrate thus obtained isdiluted with water to the concentration desired in each case.

About 20 Lucilia cuprina resistant larvae are introduced into a testtube which contains about 1 cm² of horse meat and 0.5 ml of thepreparation of active compound. After 24 hours the degree of destructionis determined.

100% means that all the larvae have been killed, 0% means that none ofthe larvae have been killed.

In this test, a degree of destruction of 100% was shown, for example, bythe compound of Preparation Example 60 at an exemplary active compoundconcentration of 1000 ppm.

Example J

Fly test

Test animals: Musca domestica, strain WHO (N)

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with seven parts of the above-mentionedsolvent/emulsifier mixture, and the resulting emulsion concentrate isdiluted with water to the particular concentration desired.

2 ml of this preparation of active compound are pipetted onto filterpaper discs (.O slashed. 9.5 cm) located in Petri dishes of suitablesize. After the filter discs have dried, 25 test animals are transferredinto the Petri dishes and covered.

After 24 hours, the effectiveness of the preparation of active compoundis determined. The effectiveness is expressed as a percentage. 100%means that all flies have been killed; 0% means that none of the flieshave been killed.

In this test, an effectiveness of 100% was shown, for example, by thecompound of Preparation Example 60 at an exemplary active compoundconcentration of 1000 ppm.

Example K

Cockroach test

Test animals: Periplaneta americana

Solvent: 35 parts by weight of ethylene glycol monomethyl ether

Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

To produce a suitable formulation, three parts by weight of activecompound are mixed with seven parts of the abovementionedsolvent/emulsifier mixture, and the resulting emulsion concentrate isdiluted with water to the particular concentration desired.

2 ml of this preparation of active compound are pipetted onto filterpaper discs (.O slashed. 9.5 cm) located in Petri dishes of a suitablesize. After the filter discs have dried, 5 test animals in B. germanicaor P. americana are transferred and covered.

After 3 days, the effectiveness of the preparation of active compound isdetermined. The effectiveness is expressed as a percentage. 100% meansthat all cockroaches have been killed; 0% means that none of thecockroaches have been killed.

At an exemplary concentration of 1000 ppm, the active compound ofPreparation Example 60 results in a destruction rate of 100%.

We claim:
 1. A compound of the formula ##STR140##
 2. A compound of theformula ##STR141##
 3. A compound of the formula ##STR142##
 4. Apesticidal composition which comprises a compound according to claim 1and an inert carrier.
 5. A pesticidal composition which comprises acompound according to claim 2 and an inert carrier.
 6. A pesticidalcomposition which comprises a compound according to claim 3 and an inertcarrier.
 7. A method of combating animal pest which comprises applying acompound according to claim 1 to said pests or to an environment wherethey reside.
 8. A method of combating animal pest which comprisesapplying a compound accordint to claim 2 to said pest or to anenvionment where they reside.
 9. A method of combating animal pest whichcomprises applying a compound accordint to claim 3 to said pest or to anenvionment where they reside.